159551-89-0

Basic information

• Product Name: (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester
• Synonyms: (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester
• CAS NO: 159551-89-0
• Molecular Weight: 337.375
• Mol File: 159551-89-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester(159551-89-0)
• EPA Substance Registry System: (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester(159551-89-0)

Safety Data

• Hazardous Substances Data: 159551-89-0(Hazardous Substances Data)

Upstream product

• 1426534-95-3 N-Cbz-trans-4-methylxanthate-L-proline 
• 1426534-96-4 N-Cbz-trans-4-methylxanthate-L-proline benzyl ester 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 159551-87-8 (2S,4R)-N^α-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester 
• 501-53-1 benzyl chloroformate 
• 13500-53-3 N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester 
• 159551-88-9 dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate 
• 100-39-0 benzyl bromide 
• 161813-74-7 (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-benzyl ester 
• 4043-88-3 3,4-dehydro-L-proline 

Downstream Products

• 159551-90-3 (1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 202473-18-5 (2S,3S,4R)-3-hydroxy-4-aminoproline 
• 202473-18-5 (2S,3R,4S)-3-hydroxy-4-aminoproline 
• 654083-19-9 (2S,3RS,4SR)-3,4-dihydroxyproline 
• 202473-19-6 (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester 
• 202473-17-4 (2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester 
• 202473-20-9 (2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester 
• 1386459-21-7 (2S,3R,4R)-3-hydroxy-4-methoxy-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 1426535-08-1 N-Cbz-cis-3-hydroxy-trans-4-isopropoxy-L-proline benzyl ester 
• 1426535-09-2 N-Cbz-trans-3-hydroxy-cis-4-benzyloxy-L-proline benzyl ester 
• 159551-91-4 dibenzyl (2S,3R,4S)-3,4-dihydroxypyrrolidine-1,2-dicarboxylate 
• 159651-34-0 (1S,2S,5R)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 95341-64-3 (2S,3R,4S)-3,4-dihydroxypyrrolidine-2-carboxylic acid 
• 202473-13-0 (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester 

Relevant articles and documents

Scaling the Amphiphilic Character and Antimicrobial Activity of Gramicidin S by Dihydroxylation or Ketal Formation

The acid lability of aliphatic ketals, which often serve as protection groups for 1,2-diols, is influenced by their local structural environment. The acetonide of the protected amino acid cis-dihydroxyproline (Dyp) is a typical protecting group cleavable by traces of TFA. The tricyclic acetonide of the dipeptide d-Hot-Tap is resistant to TFA and thus can serve as a bioorthogonal modification of bioactive peptides. With the aim of improving antimicrobial activity and hemolytic properties, we use these reactivity differences to scale the membrane affinity of the decapeptide Gramicidin S cyclo(d-Phe-Pro-Val-Orn-Leu-)2 (GS). The cis-dihydroxylated amino acids are used to increase the polarity of GS or obversely decrease the polarity by stereoselective ketal formation with an aliphatic ketone. While Dyp (GS mimetic 15) has only minimal influence on the biological properties of GS, d-Hot-Tap at the position of d-Phe1-Pro2 eradicates the biological activity (GS mimetic 16). The acid-stable ketals 17-19 are bioorthogonal modifications which reconstitute the biological activity of GS. We describe an improved synthesis of orthogonally protected Fmoc-Dyp-acetonide (9) and of several Fmoc-d-Hot-Tap-ketals for solid-phase peptide synthesis.

PYRROLIDINE DERIVATIVES AND THEIR USE AS COMPLEMENT PATHWAY MODULATORS

The present invention provides a compound of formula I: (I) a method for manufacturing the compounds of the invention, and its therapeutic uses as complement alternative inhibitors for the treatment of ocular diseases. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

PYRROLIDINE DERIVATIVES AND THEIR USE AS COMPLEMENT PATHWAY MODULATORS

The present invention provides a compound of formula (I) a method for manufacturing the compounds of the invention, and its therapeutic uses as a factor D inhibitor for the treatment of ophthalmic diseases. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.